The Worst Free Agent Signings in NHL History

NHL free agency generates a large amount of excitement throughout the hockey world every year.

In some cases, an NHL team will make a great signing, acquiring a player through a low term, low paying contract who brings unexpected results and production to his new team.

On the other hand, NHL teams may sign a player to a long term contract which pays an extremely high yearly salary. For whatever reason, these contracts tend to be the least successful, as teams tend to get less than desired production and results from these players who have expectations of greatness placed upon them.

The following five players are among the most infamous free agent signings in NHL history.

Bobby Holik: Free Agent for the New York Rangers

In 2002, Glen Sather signed free agent Bobby Holik to what turned out to be one of the worst contracts in NHL history.

Bobby Holik (Brooke Novak, Flickr)

Holik, who had always been a relatively average NHL player during his previous 12 seasons, had just finished up his time with the New Jersey Devils, a team with which he had spent his last 10 years. During his time with the Devils, Holik had never scored more than 30 goals, and never amassed greater than 65 points in a season. In his final season with the Devils, Holik was paid $3.5 million, which was considered high given his average offensive production.

However, prior to the 2002-03 season, Sather signed Holik to a five year, 45 million dollar contract. The contract had an average annual salary of nine million dollars!

The contract was so ridiculous that there was literally no chance for Holik to justify his pay. In his first season with the Rangers, which saw him paid $9.6 million, Holik scored a mere 16 goals and 35 points. $9.6 million for 35 points! Holik was paid an incredible $274 thousand per point he scored. His 2003-04 season was somewhat better, scoring 25 goals and 56 points, but his output remained nowhere near the $8.9 million he was paid during his second season in New York.

After two seasons, Sather, amidst a salary cap crunch, finally realized what a terrible signing Bobby Holik had been, subsequently buying out his contract.

Sheldon Souray: Free Agent for the Edmonton Oilers

In the 2007 offseason, the Edmonton Oilers went shopping for a star defenseman. They found their man in Sheldon Souray, signing him to a five year contract worth $27 million dollars.

Souray had spent the first nine seasons of his career between the New Jersey Devils and Montreal Canadiens and was coming off of a huge year with the Canadiens. He had scored 26 goals and 64 points in 81 games during the 2006-07 season, his final with the Canadiens, which he parlayed into a huge contract with the Oilers. Yet prior to his breakout season, Souray had played average hockey and was highly injury prone, missing significant portions of time, including the entire 2002-03 season.

Sheldon Souray with the Edmonton Oilers

In his first season with the Oilers, Souray was slated to make $6.25 million dollars. However, similar to the majority of his career to that point, the Edmonton native was once again hampered by injuries. Sheldon ended up playing in only 26 games with the Oilers in the 2007-08 season, in which he only scored three goals and 10 points. Souray’s second season was his only successful campaign with the Oilers, in which he managed to play 81 games, scoring 23 goals, 53 points and was named an All-Star. It was the only season in which the Oilers got what they had paid for.

The following 2009-10 season witnessed much of the same from Souray, who once again battled a multitude of injuries. Due to an early concussion followed by a hand injury which later became infected, Souray was only able to play in 37 games. In his third season with the Oilers, Souray scored a mere 13 points and had a disastrous -19 plus/minus rating, emphasising the chronic frustration which characterized Souray’s time in Edmonton.

Prior to the 2010-11 season, Souray demanded a trade from the Oilers, but due to his high cap hit and inability to stay healthy, no teams were interested in his services. Unable to trade Souray, the Oilers eventually put Sheldon on waivers before he was loaned to the Hershey Bears of the AHL. Souray finished the year with the Bears before the Oilers finally bought out his contract in the summer of 2011, forced to pay Souray $3 million dollars over two years to not play on their team.

Jeff Finger: Free Agent for the Toronto Maple Leafs

As has long been the case, the Toronto Maple Leafs were looking to upgrade their blue-line through free agency in the summer of 2008. In order to address their need, the Leafs signed Jeff Finger to a four year contract worth $14 million dollars.

Jeff Finger (James Teterenko, Wikipedia)

Having only played one full season in the NHL before signing with the Leafs, it is a wonder as to why Toronto offered $3.5 million per season to a player who had yet to prove his place in the NHL. Finger had spent two seasons with the Avalanche, playing 22 games in 2006-07 and 71 games in 2007-08. In those 93 career NHL games, Finger had only scored 24 points, but was becoming known league wide for his strong defensive play.

When the 2008-09 season finally began, the Leafs were hoping Finger would be a strong defensive defenseman. In 66 games, Finger set his NHL career high with 23 points, yet failed to live up to the hype in terms of his strong play in the defensive end, play which found Finger watching the Leafs from the press box on more than a few occasions. In his second season, Finger effectively played himself out of the lineup. His poor play limited him to 39 games with Leafs, in which he contributed 10 points.

Eventually, the Leafs chose to waive Finger, sending him to the minors where he played parts of two seasons with the Toronto Marlies. In those two seasons, Finger played 23 and 31 games, the last of his professional hockey career.

Wade Redden: Free Agent for the New York Rangers

When the 2008 free agency period began, the New York Rangers wasted no time in signing Wade Redden to a six year contract, worth $39 million.

Wade Redden while with the New York Rangers

Redden had become known as one of the better defenseman in the NHL, and as a result was a highly sought after player by many teams. Wade had played all previous 11 years of his NHL career with the Ottawa Senators, with which he was a force both offensively and defensively. On top of a strong game in his own end, Redden was a consistent contributor, scoring 101 goals and 410 points in his 838 games with the Senators.

In Redden’s first season with the Rangers, he had an average year to his standard, scoring 26 points in 81 games, his lowest point total in the past ten years of his career. In 2009-10, his second season, Redden saw a continued regression in his game, producing two goals and 14 points over 75 games. By this point, Rangers fans had become vastly irritated with Redden, as his play was nowhere near worth the $8 million dollars he was paid in each of his first two seasons.

The following season, Redden was waived and played each of the next two season with the Connecticut Whale of the AHL. The decision allowed the Rangers to remove the burden of Redden’s salary off of their salary cap.

In 2012-13, Redden had his contract bought out by the Rangers. New York elected to pay Wade upwards of $3 million dollars over a three year period for him to not play within their organization. Redden, who has now been out of professional hockey for the past two seasons, will still be paid $1.6 million during this, the 2014-15 season.

Brad Richards: Free Agent for the New York Rangers

In 2011, the New York Rangers made what turned out to be yet another terrible free agent signing, securing the services of Brad Richards for nine years, at a cost of $60 million dollars.

Richards, who entered free agency following a five year, $39 million dollar contract with the Dallas Stars, was the most sought after player available in 2011 free agency. A proven number one center, Richards attracted league wide interest before deciding to sign the Rangers.

In years prior, Richards had been a consistent player offensively. While with the Tampa Bay Lightning, Richards scored 489 points in 552 games, alongside winning the Lady Byng, Conn Smythe and also the Stanley Cup. With Dallas, Richards’ game continued to improve, scoring over a point per game with 227 points in 220 contests. Yet everything changed for Richards in his first season in the big apple.

Brad Richards with the Rangers

Earning a whopping $12 million dollar salary, which included a $10 million dollar signing bonus, Richards had an average season, one which was poor compared to his standards. Scoring 25 goals in 2011-12, Richards totaled 66 points, his lowest total in a full season since his sophomore year the Lightning. Richards’ second season with the Rangers was even less impressive, as Brad was limited to 34 points over 46 games in a lock-out shortened campaign. Although his points per game was up slightly, his 11 goals were less than impressive.

In 2013-14, Richards’ third season with the Rangers, the situation got even worse. Brad was only able to score 20 goals, his lowest goal total in a full season in the past 10 years. The 51 points he scored was the lowest full season total of his career, play which certainly did not warrant a $9 million dollar salary.

After being demoted to the team’s fourth line in the playoffs and rumors swirling that he would be made a healthy scratch, Richards was bought out by the Rangers at the end of the 2013-14 season.

The decision to buy out Richards meant that Brad would remain on the Rangers’ books for the next 12 seasons, until the year 2025-26! During this immense stretch of time, Richards is owed an unimaginable $20.6 million dollars to not play for the Rangers.

Brad Richards’ contract will certainly go down in history as one of the worst free agent signings of all time.

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